1,3-Dibromopropane → HCID 86686569, compound

HRID 1528089Notes

Reaction equation

HRID 1528089 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].Br[CH2:19][CH2:20][CH2:21]Br.[Cl-].[NH4+]>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[C:13]1([C:14]([O:16][CH3:17])=[O:15])[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86686570HCID 86686570, compound

Product 1

HCID 86686569HCID 86686569, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium hydride (9.49 g) in DMF (75 mL) was added dropwise a solution of methyl (2-fluoro-6-nitrophenyl)acetate (23 g) and 1,3-dibromopropane (13.1 mL) in DMF (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 4 hr, cooled to 0° C. Saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (11.3 g).

Workup

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-823b249abc8e43acad509323b50b7815
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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